Methyl benzyloxycarbonyl-l-tyrosyl-l-valyl-l-alaninate → Methyl l-tyrosyl-l-valyl-l-alaninate

HRID 1357461Notes

Reaction equation

HRID 1357461 reaction equation
C(OC([NH:11][C@H:12]([C:21]([NH:23][C@H:24]([C:28]([NH:30][C@H:31]([C:33]([O:35][CH3:36])=[O:34])[CH3:32])=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=O)C1C=CC=CC=1>CN(C)C=O.[Pd]>[NH2:11][C@H:12]([C:21]([NH:23][C@H:24]([C:28]([NH:30][C@H:31]([C:33]([O:35][CH3:36])=[O:34])[CH3:32])=[O:29])[CH:25]([CH3:26])[CH3:27])=[O:22])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 69531229Methyl benzyloxycarbonyl-l-tyrosyl-l-valyl-l-alaninate

Product 1

HCID 53888084Methyl l-tyrosyl-l-valyl-l-alaninate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

2.99 g (6.0 mmol) of methyl benzyloxycarbonyl-L-tyrosyl-L-valyl-L-alaninate (Example 1, Step A2) are dissolved in 30 ml of dimethylformamide, 0.2 g of Pd/C catalyst is added, then the mixture is submitted to hydrogenation at about 20° C. The catalyst is filtered off and the filtrate is evaporated at a pressure of 2.0-2.5 kPa. The residue is rubbed with diethyl ether, filtered, washed with diethyl ether and dried in a vacuum desiccator.

Workup

  1. customis submitted to hydrogenation at about 20° C
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated at a pressure of 2.0-2.5 kPa
  4. filtrationfiltered
  5. washwashed with diethyl ether
  6. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-f8b1c7ee6c3e48289251784fd3ed0972
Source dataset
uspto-grants-2003_07
Patent number
US06593300B1

Reaction notes

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